EP0345111A2 - Oberflächenaktiver Stoff auf der Basis von oxyethylierten und oxypropylierten Phenyl-1-ethylphenolen, Verfahren zu ihrer Herstellung und ihre Verwendung zum Erhalten von konzentrierten Lösungen von aktiven Verbindungen - Google Patents

Oberflächenaktiver Stoff auf der Basis von oxyethylierten und oxypropylierten Phenyl-1-ethylphenolen, Verfahren zu ihrer Herstellung und ihre Verwendung zum Erhalten von konzentrierten Lösungen von aktiven Verbindungen Download PDF

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Publication number
EP0345111A2
EP0345111A2 EP89401340A EP89401340A EP0345111A2 EP 0345111 A2 EP0345111 A2 EP 0345111A2 EP 89401340 A EP89401340 A EP 89401340A EP 89401340 A EP89401340 A EP 89401340A EP 0345111 A2 EP0345111 A2 EP 0345111A2
Authority
EP
European Patent Office
Prior art keywords
units
formula
approximately
surfactant
ratio
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP89401340A
Other languages
English (en)
French (fr)
Other versions
EP0345111A3 (en
EP0345111B1 (de
Inventor
Antonio Marchetto
Anghelito Mascheroni
Georges Ruffo
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Rhone Poulenc Geronazzo SpA
Original Assignee
Rhone Poulenc Geronazzo SpA
Geronazzo SpA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Rhone Poulenc Geronazzo SpA, Geronazzo SpA filed Critical Rhone Poulenc Geronazzo SpA
Publication of EP0345111A2 publication Critical patent/EP0345111A2/de
Publication of EP0345111A3 publication Critical patent/EP0345111A3/fr
Application granted granted Critical
Publication of EP0345111B1 publication Critical patent/EP0345111B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/42—Ethers, e.g. polyglycol ethers of alcohols or phenols
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
    • C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
    • C08G65/2612—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aromatic or arylaliphatic hydroxyl groups
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
    • Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
    • Y10S516/03—Organic sulfoxy compound containing
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
    • Y10S516/905—Agent composition per se for colloid system making or stabilizing, e.g. foaming, emulsifying, dispersing, or gelling
    • Y10S516/917—The agent contains organic compound containing oxygen
    • Y10S516/92—The compound contains repeating unsubstituted oxyalkylene

Definitions

  • the subject of the present invention is a surfactant based on poly (1-phenylethyl) phenols carrying statistically distributed polyoxyethylenated and polyoxypropylenated units, its process of preparation and its application to obtaining concentrated emulsifiable solutions of active materials which are then diluted to obtain ready-to-use emulsions.
  • biocidal compositions capable of being dispersed in water using surfactants of the tri (1-phenylethyl) type polyoxyethylenated phenols or carrying polyoxyethylenated and polyoxypropylenated units distributed in a sequenced manner ( Japanese application published under No. 25526/1975).
  • the Applicant has found a surfactant soluble in this type of solvent.
  • the surfactant which is the subject of the invention consists of at least one poly (1-phenylethyl) phenol poly-oxyethylenated and -oxypropylenated of formula (I) below: formula in which: . m is 2 or 3 .
  • (OX) n represents a statistical succession of oxyethylenated units and oxypropylenated units . n being such that the total number of oxyalkylene units of the radical (OX) n ranges from approximately 16 to approximately 35, and preferably from 20 to 30, with a ratio of number of oxyethylene units / number of oxypropylene units ranging from approximately 75 / 25 to 90/10 and preferably from 80/20 to 90/10.
  • the surfactant which is the subject of the invention can be obtained by the action of at least one poly (1-phenylethyl) phenol of formula (II): and of a mixture of monoethylene glycol and monopropylene glycol according to a monoethylene glycol / monopropylene glycol ratio corresponding to the ratio number of oxyethylenated units / number of oxypropylenated units sought.
  • This operation is carried out for a period of the order of 20 to 40 minutes at a temperature of 140-180 ° C., in the presence of 0.5 to 1.5% by weight relative to the finished product of an alkaline base, such as sodium hydroxide, as a catalyst.
  • an alkaline base such as sodium hydroxide
  • the present invention also relates to concentrated emulsifiable solutions obtained by formulation of active materials soluble in organic solvents using the surfactant which is the subject of the invention.
  • active ingredients capable of forming concentrated emulsifiable solutions mention may be made of insecticides, acaricides, fungicides and their various combinations, herbicides, nematicides, molluscicides, attractants, repellents, rodenticides.
  • insecticides suitable for the invention mention may be made of those which belong to families: - organo-halogenated or chlorinated; - carbinols; - organophosphates; - sulfones and sulfonates; - carbamates; - benzoyl ureas; - synthetic pyrethrinoids.
  • the fungicides capable of being used in the invention can be chosen from: - carbamates; - benzene derivatives; - phenol derivatives; - quinones; - dicarboximides; - amines, amides; - diazines - sulfonamides and sulfur derivatives; - guanidines; - heterocyclic compounds; - metallic monoethyl phosphites; - organotin.
  • Concentrated emulsifiable solutions are favorably constituted: - at least one active ingredient - an organic solvent for said active material - the surfactant of the invention optionally added with one or more anionic (cation), cationic (s), nonionic (s) or amphoteric (s) surfactant (s) in this type of application - any wetting agent - possibly a stabilizer - and various additives.
  • the organic solvents which can be used are those usually used in this type of formulation.
  • aromatic hydrocarbons cyclohexanone, methylhexahydronaphthalene, tetrahydronaphthalene dimethyl sulfoxide, dimethyl formamide, dibutyl phthalate, isophorone, N-methylpyrrolidone, butyrolactone ...
  • the said solvent can optionally be removed if the active material used is liquid at a temperature of -20 to 50 ° C.
  • the surfactant of the invention has in itself a wetting power; therefore the presence of a wetting agent is not essential; if however the presence of such an agent is desired, the latter may be chosen by the following: - alkali metal soaps such as sodium or potassium salts of C gras-C24 saturated or unsaturated fatty acids, sodium N-lauryl sarcosinate, sodium N-acylsarcosinate - alkaline sulfonates such as alkyl sulfonates of the sodium diethylhexylsulfocuccinate type; alkylbenzene sulfonates of the nonyl- or dodecyl-benzenesulfonate type of sodium, diethanolamine, triethanolamine or N-methylcyclohexylamine; alkali alkylnaphthalene sulfonates; alkaline N-alkylltaurates - sulphates and sulphated products such as alkali metal sulphates of
  • organic acids chosen from optionally halogenated aliphatic monocarboxylic acids (formic, monochloroacetic, propionic, citric, tartaric, etc.), aliphatic hydroxycarboxylic (glycolic, etc.) aromatic (benzoic , phthalic %) optionally substituted (dichlorobenzoic, dimethoxybenzoic, hydroxybenzoic, dihydroxybenzoic, nitrobenzoic, nitroisophthalic Among the optional stabilizers which can be used, mention may be made of organic acids chosen from optionally halogenated aliphatic monocarboxylic acids (formic, monochloroacetic, propionic, citric, tartaric, etc.), aliphatic hydroxycarboxylic (glycolic, etc.) aromatic (benzoic , phthalic 7) optionally substituted (dichlorobenzoic, dimethoxybenzoic, hydroxybenzoic, dihydroxybenzoic, nitrobenzoic,
  • additives are understood to mean the other ingredients or additives customary in the formulation of agricultural products, in particular penetrating agents, corrosion inhibitors, adhesives, etc.
  • the weight proportions of the various constituents of concentrated emulsifiable solutions are generally as follows: - from 0.1 to 90 parts by weight of active material - from 0.5 to 25 parts by weight of surfactant of the invention - from 0 to 25 parts of wetting agent - and the complement to 100 parts in organic solvent.
  • a surfactant is prepared, the characteristics of which are given in Table I, according to the preparative mode of Example 1.
  • Emulsifiable concentrates are prepared from different active materials, according to the following process:
  • the active ingredient is dissolved in xylene and then a surfactant (TA) forming the subject of one of Examples 2 to 16 and calcium dodecylbenzene sulfonate (CaDDBS) is added.
  • TA surfactant
  • CaDDBS calcium dodecylbenzene sulfonate
  • the stability of the emulsions in water prepared from these compositions is measured according to the CIPAC MT 36.1 method in standardized waters A (20 ppm hardness), D (342 ppm hardness) and C (500 ppm hardness) after 60 minutes of 120 minutes.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • Wood Science & Technology (AREA)
  • Agronomy & Crop Science (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Organic Chemistry (AREA)
  • Toxicology (AREA)
  • Zoology (AREA)
  • Dentistry (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Materials Engineering (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Polyethers (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP89401340A 1988-05-27 1989-05-12 Oberflächenaktiver Stoff auf der Basis von oxyethylierten und oxypropylierten Phenyl-1-ethylphenolen, Verfahren zu ihrer Herstellung und ihre Verwendung zum Erhalten von konzentrierten Lösungen von aktiven Verbindungen Expired - Lifetime EP0345111B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT20777/88A IT1219699B (it) 1988-05-27 1988-05-27 Agente tensio attivo a base di (fenil 1 etil) fenoli poliossialchilenati,suo procedimento di preparazione e suo impiego per ottenere soluzioni concentrate emulsionabili di sostanze attive
IT2077788 1988-05-27

Publications (3)

Publication Number Publication Date
EP0345111A2 true EP0345111A2 (de) 1989-12-06
EP0345111A3 EP0345111A3 (en) 1990-05-23
EP0345111B1 EP0345111B1 (de) 1993-07-21

Family

ID=11171913

Family Applications (1)

Application Number Title Priority Date Filing Date
EP89401340A Expired - Lifetime EP0345111B1 (de) 1988-05-27 1989-05-12 Oberflächenaktiver Stoff auf der Basis von oxyethylierten und oxypropylierten Phenyl-1-ethylphenolen, Verfahren zu ihrer Herstellung und ihre Verwendung zum Erhalten von konzentrierten Lösungen von aktiven Verbindungen

Country Status (7)

Country Link
US (1) US5082591A (de)
EP (1) EP0345111B1 (de)
JP (1) JPH0661440B2 (de)
AU (1) AU617809B2 (de)
CA (1) CA1307010C (de)
DE (1) DE68907650T2 (de)
IT (1) IT1219699B (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5772920A (en) * 1995-07-12 1998-06-30 Clariant Finance (Bvi) Limited U.V. absorber compositions

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HU206241B (en) * 1989-05-08 1992-10-28 Chinoin Gyogyszer Es Vegyeszet Plant protective and additive compositions comprising citric acid and tartaric acid derivatives and process for producing veterinary compositions
FR2673075B1 (fr) * 1991-02-22 1998-12-31 Rhone Poulenc Chimie Microemulsions de pyrethrouides et leur utilisation.
CA2157691C (en) * 1994-09-29 1998-08-18 Joseph Doolan High performance alkali-swellable rheological additives for aqueous systems
US5874495A (en) * 1994-10-03 1999-02-23 Rhodia Inc. Polymers useful as PH responsive thickeners and monomers therefor
US5906962A (en) * 1994-12-22 1999-05-25 Rhodia Inc. Non-aqueous suspension concentrates of highly water-soluble solids
US5707551A (en) * 1994-12-22 1998-01-13 Rhone-Poulenc Inc. Nonaqueous suspension concentrates of highly water-soluble solids
US5981433A (en) * 1995-06-29 1999-11-09 Rhone-Poulenc Chimier Lignosulfonate/ethoxylated poly(1-phenylethyl)phenol dispersing agents and agrochemicals comprised thereof
JPH10143977A (ja) 1996-09-10 1998-05-29 Sony Corp ディスク装置およびそれを用いたビデオカメラ装置
WO2000073382A1 (fr) * 1999-05-28 2000-12-07 Jsr Corporation Emulsion d'elastomere thermoplastique et son procede de production
KR101424829B1 (ko) * 2006-03-24 2014-08-01 바스프 에스이 농약 제제
US9388323B2 (en) * 2008-01-18 2016-07-12 Rhodia Operations Latex binders, aqueous coatings and paints having freeze-thaw ability and methods for using same
JP5596557B2 (ja) * 2008-01-18 2014-09-24 ロディア オペレーションズ ラテックスバインダー、凍結融解安定性を有する水性コーティング及び塗料並びにそれらの使用法
US9109152B2 (en) * 2009-09-10 2015-08-18 Board Of Regents, The University Of Texas System Compositions and methods for controlling the stability of ethersulfate surfactants at elevated temperatures
CN102652163B (zh) * 2009-12-11 2015-07-15 罗地亚管理公司 改善乳胶粘连剂和水性涂料的开放时间和干燥时间的方法和系统
WO2011094442A1 (en) * 2010-01-28 2011-08-04 Board Of Regents, The University Of Texas System Styrylphenol alkoxylate sulfate as a new surfactant composition for enhanced oil recovery applications
CN105386364B (zh) * 2014-09-04 2018-02-06 瑞辰星生物技术（广州）有限公司 制浆造纸生产中降低和去除有机污染物沉积及油墨的方法

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FR2452250A1 (fr) * 1979-03-28 1980-10-24 Kao Corp Composition pesticide fluide et son procede de preparation
EP0025139A2 (de) * 1979-08-29 1981-03-18 Bayer Ag Wässrige Dispersionen von Epoxidverbindungen
EP0055401A1 (de) * 1980-12-19 1982-07-07 Bayer Ag Insektizide und akarizide Mittel und ihre Verwendung
EP0341126A1 (de) * 1988-05-04 1989-11-08 Rhone-Poulenc Chimie Oberflächenaktive Zusammensetzungen auf Basis von polyoxyalcoylenierten Poly(phenyl-1-äthyl)phenolphosphorsäureestern, ihr Verfahren zur Herstellung und ihre Verwendung zum Erhalten von wässerigen Dispersionen von aktiven Substanzen
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Publication number Priority date Publication date Assignee Title
FR2234265A1 (de) * 1973-06-20 1975-01-17 Montedison Spa
GB2007692A (en) * 1977-11-02 1979-05-23 Rhone Poulenc Ind Anti-soiling and anti-redesposition compositions which can be used in detergency
FR2452250A1 (fr) * 1979-03-28 1980-10-24 Kao Corp Composition pesticide fluide et son procede de preparation
EP0025139A2 (de) * 1979-08-29 1981-03-18 Bayer Ag Wässrige Dispersionen von Epoxidverbindungen
EP0055401A1 (de) * 1980-12-19 1982-07-07 Bayer Ag Insektizide und akarizide Mittel und ihre Verwendung
EP0341126A1 (de) * 1988-05-04 1989-11-08 Rhone-Poulenc Chimie Oberflächenaktive Zusammensetzungen auf Basis von polyoxyalcoylenierten Poly(phenyl-1-äthyl)phenolphosphorsäureestern, ihr Verfahren zur Herstellung und ihre Verwendung zum Erhalten von wässerigen Dispersionen von aktiven Substanzen
JPH0525526A (ja) * 1991-07-16 1993-02-02 Kawasaki Steel Corp 溶銑の脱硫方法

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5772920A (en) * 1995-07-12 1998-06-30 Clariant Finance (Bvi) Limited U.V. absorber compositions

Also Published As

Publication number Publication date
CA1307010C (fr) 1992-09-01
EP0345111A3 (en) 1990-05-23
JPH02157031A (ja) 1990-06-15
IT1219699B (it) 1990-05-24
AU617809B2 (en) 1991-12-05
EP0345111B1 (de) 1993-07-21
DE68907650T2 (de) 1994-01-27
IT8820777A0 (it) 1988-05-27
JPH0661440B2 (ja) 1994-08-17
US5082591A (en) 1992-01-21
AU3520289A (en) 1989-11-30
DE68907650D1 (de) 1993-08-26

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